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Deoxypodophyllotoxin

Names

[ CAS No. ]:
19186-35-7

[ Name ]:
Deoxypodophyllotoxin

[Synonym ]:
(5R,5aR,8aR)-5-(3,4,5-Trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Anthricin
deoxypodophyllotoxin
Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)-
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)-

Biological Activity

[Description]:

Deoxypodophyllotoxin (DPT), a derivative of podophyllotoxin, is a lignan with potent antimitotic, anti-inflammatory and antiviral properties isolated from rhizomes of Sinopodophullumhexandrum (Berberidaceae). Deoxypodophyllotoxin, targets the microtubule, has a major impact in oncology not only as anti-mitotics but also as potent inhibitors of angiogenesis[1]. Deoxypodophyllotoxin induces cell autophagy and apoptosis[2]. Deoxypodophyllotoxin evokes increase of intracellular Ca2+ concentrations in DRG neurons[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cardiovascular Disease
Research Areas >> Infection
Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin
Signaling Pathways >> Autophagy >> Autophagy
Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[In Vitro]

Deoxypodophyllotoxin (25-75 nM; 6-48 hours) increases the percentage of early apoptotic cell population from 2.05 to 5.62 and 18.49% for 24 h and 48 h, respectively[1]. Deoxypodophyllotoxin (25-75 nM; 6-48 hours) treats SGC-7901 cells arrested in G2/M phase in time- and dose- dependent manners[1]. Deoxypodophyllotoxin (25-75 nM; 6-48 hours) results in a remarkably time- and dose-dependent decrease in Cdc2 and Cdc25C expression levels and increases cyclin B1 within 6h, decreases PARP, Bcl-2 and caspase-3 activity[1]. Apoptosis Analysis[1] Cell Line: SGC-7901 cells Concentration: 25, 50, 75 nM Incubation Time: 6, 12, 24, 48 hours Result: Induced apoptosis in SGC-7901 Cells. Cell Cycle Analysis[1] Cell Line: SGC-7901 cells Concentration: 25, 50, 75 nM Incubation Time: 6, 12, 24, 48 hours Result: Induced G2/M cell cycle arrest in SGC-7901 Cells Western Blot Analysis[1] Cell Line: SGC-7901 cells Concentration: 25, 50, 75 nM Incubation Time: 6, 12, 24, 48 hours Result: Altered the expression of cyclin B1, Cdc2,Cdc25C, p-PARP, Bcl-2 and p-caspase-3 proteins.

[In Vivo]

Deoxypodophyllotoxin (intravenously injected; 5, 10, and 20 mg/kg; 3 times a week; 28 days) suppresses the tumors in a dose-dependent manner, the growth of tumors is inhibited by 22.19%, 47.91% and 50.93% with DPT at 5, 10 and 20 mg/kg, respectively[1]. Animal Model: Xenograft model of gastric cancer in nude mice with SGC-7901 cells[1] Dosage: 5, 10, and 20 mg/kg Administration: Intravenously injected; 5, 10, and 20 mg/kg; 3 times a week; 28 days Result: Inhibited the growth of gastric cancer tumors.

[References]

[1]. Wang YR, et al. Deoxypodophyllotoxin induces G2/M cell cycle arrest and apoptosis in SGC-7901 cells and inhibits tumor growth in vivo. Molecules. 2015 Jan 20;20(1):1661-75.

[2]. Kim SH, et al. Deoxypodophyllotoxin induces cytoprotective autophagy against apoptosis via inhibition of PI3K/AKT/mTOR pathway in osteosarcoma U2OS cells. Pharmacol Rep. 2017 Oct;69(5):878-884.

[3]. Xu P, et al. Pharmacological effect of deoxypodophyllotoxin: a medicinal agent of plant origin, on mammalian neurons. Neurotoxicology. 2010 Dec;31(6):680-6.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
564.5±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C22H22O7

[ Molecular Weight ]:
398.406

[ Flash Point ]:
247.0±30.2 °C

[ Exact Mass ]:
398.136566

[ PSA ]:
72.45000

[ LogP ]:
2.44

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.587

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TP9002800
CHEMICAL NAME :
Podophyllotoxin, deoxy-
CAS REGISTRY NUMBER :
19186-35-7
LAST UPDATED :
198702
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C22-H22-O7
MOLECULAR WEIGHT :
398.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Human HeLa cell
DOSE/DURATION :
500 nmol/L
REFERENCE :
BICHAW Biochemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1962- Volume(issue)/page/year: 15,5443,1976

Safety Information

[ Hazard Codes ]:
Xi


Related Compounds